Patent application title: PROCESS FOR PRODUCING HYDROLYZATE

Abstract:

In a method for producing a hydrolysate in which an organic compound and
water are mixed and a hydrolysis reaction of the organic compound is
performed, shear flow of the organic compound and the water at a shear
rate U/Dmin of 5.5 sec-1 or more (where Dmin is a flow channel
minimum inner diameter (mm) in a mixing section and U is a flow rate
(mm/sec) of a mixture of the organic compound and the water in the mixing
section), thereby mixing the organic compound and the water, and the
hydrolysis reaction of the organic compound is performed at a reaction
temperature of 150° C. to 350° C. and a reaction pressure
equal to or higher than a saturation vapor pressure of the water.

Claims:

1. A method for producing a hydrolysate in which an organic compound and
water are mixed and a hydrolysis reaction of the organic compound is
performed,wherein the mixing is performed under shear flow of the organic
compound and the water at a shear rate U/Dmin of 5.5 sec-1 or more
(where Dmin is a flow channel minimum inner diameter (mm) in a mixing
section and U is a flow rate (mm/sec) of a mixture of the organic
compound and the water in the mixing section), andthe hydrolysis reaction
of the organic compound is performed at a reaction temperature of
150.degree. C. to 350.degree. C. and a reaction pressure equal to or
higher than a saturation vapor pressure of the water.

2. The method of claim 1, wherein the hydrolysis reaction of the organic
compound is performed without using a catalyst.

3. The method of claim 1, wherein the mixing of the organic compound and
the water and the hydrolysis reaction of the organic compound are
simultaneously performed.

4. The method of claim 1, wherein after mixing the organic compound and
the water, the hydrolysis reaction of the organic compound is
subsequently performed.

5. The method of claim 1, wherein the hydrolysis reaction of the organic
compound is a ring-opening reaction by the water.

6. The method of claim 1, wherein the organic compound is glycidyl ether
expressed by a general formula (1) ##STR00002## (where R is a hydrocarbon
group in which part or all hydrogen atoms may be replaced with fluorine
atoms, of which carbon number is 1 to 20 and which is saturated or
unsaturated, OA is an oxyalkylene group which may be the same as or
different from another OA and of which carbon number is 2 to 4, and p is
a number of 0 to 20).

7. The method of claim 1, wherein an amount of the water with respect to
the organic compound is, in terms of molar conversion, 20 to 500 times as
large as a stoichiometric amount of water required for the reaction.

8. The method of claim 1, wherein the hydrolysis reaction of the organic
compound is continuously performed.

9. The method of claim 1, wherein the flow channel minimum inner diameter
in the mixing section in which the organic compound and the water are
mixed is 1 mm to 15 mm.

10. The method of claim 1, wherein the organic compound and the water are
mixed by flowing the organic compound and the water through a static
mixer.

11. The method of claim 10, wherein the static mixer is a contraction flow
type mixer.

Description:

TECHNICAL FIELD

[0001]The present invention relates to a method for producing a
hydrolysate.

BACKGROUND ART

[0002]Hydrolysis reaction such as ring-opening reaction of an organic
compound and the like is industrially used in many situations. For
example, glyceryl ether obtained by ring-opening reaction of glycidyl
ether is a compound useful as a solvent, an emulsifier, a dispersant, a
detergent, a foam booster and the like.

[0003]Although glyceryl ether is produced using a catalyst in general, as
a method for producing glyceryl ether without using a catalyst, for
example, a method in which glycidyl ether is brought into a hydrolysis
reaction with subcritical water or the like has been known (see Patent
Reference 1).

[0004]However, in the known method, depending on a mixture state of an
organic compound and water, delay in reaction time, a side reaction of
dimerizing the organic compound as a raw material and a generated
hydrolysate are increased or like problems are caused.

[0006]The present invention provides a method for effectively producing a
high quality hydrolysate by making a mixture state of an organic compound
and water be a good condition for reaction.

[0007]To achieve this, the present invention is directed to a method for
producing a hydrolysate in which an organic compound and water are mixed
and a hydrolysis reaction of the organic compound is performed. In the
method, the mixing is performed under shear flow of the organic compound
and the water at a shear rate U/Dmin of 5.5 sec-1 or more (where
Dmin is a flow channel minimum inner diameter (mm) in a mixing section
and U is a flow rate (mm/sec) of a mixture of the organic compound and
the water in the mixing section), and the hydrolysis reaction of the
organic compound is performed at a reaction temperature of 150° C.
to 350° C. and a reaction pressure equal to or higher than a
saturation vapor pressure of the water.

BRIEF DESCRIPTION OF THE DRAWINGS

[0008]FIG. 1 is a diagram schematically illustrating an exemplary device
preferably used in an embodiment of a method for producing a hydrolysate
according to the present invention.

[0009]FIG. 2 is a diagram schematically illustrating another exemplary
device preferably used in an embodiment of a method for producing a
hydrolysate according to the present invention.

BEST MODE FOR CARRYING OUT THE INVENTION

[0010]The present invention is characterized in that when an organic
compound and water are mixed to perform a hydrolysis reaction of the
organic compound, under predetermined conditions, the organic compound
and water are mixed and hydrolysis of the organic compound is performed.

[0011]According to the present invention, decomposition and a side
reaction of an organic compound as a raw material can be suppressed in
the hydrolysis reaction and thus deterioration of hue of the generated
hydrolysate and the like can be prevented. Furthermore, according to the
present invention, since the hydrolysis reaction is performed under a
high temperature condition, the reaction can proceed with high
selectivity even without using a catalyst, the step of removing a
catalyst from a reactant is not necessary, and a high quality hydrolysate
can be efficiently produced.

[0012]As long as the components do not inhibit achievement of desired
effects of the present invention, components and the like described below
can be used independently or two or more of the components can be
combined and then used.

[0013]According to the present invention, an organic compound used as a
raw material is not particularly limited as long as it is a compound
which can be decomposed through hydrolysis. The hydrolysis reaction is
preferably a ring-opening reaction using water. Accordingly, an organic
compound used as a raw material is preferably a compound which has a ring
structure and of which ring structure is opened due to the hydrolysis
reaction. As such a compound, glycidyl ether expressed by the following
general formula (I) is to preferable.

##STR00001##

[0014](where R is a hydrocarbon group in which part or all hydrogen atoms
may be replaced with fluorine atoms, of which carbon number is 1 to 20
and which is saturated or unsaturated, OA is an oxyalkylene group which
may be the same as or different from another OA and of which carbon
number is 2 to 4, and p is a number of 0 through 20). Gryceryl ether
obtained by ring-opening of glycidyl ether is a compound useful as a
solvent, an emulsifier, a dispersant, a detergent, a foam booster and the
like.

[0015]In the above formula, as the hydrocarbon group denoted by R, in
which part or all hydrogen atoms may be replaced with fluorine atoms and
of which carbon number is 1 to 20, for example, a straight-chain or
branched-chain alkyl group of which carbon number is 1 to 20, a
straight-chain or branched-chain alkenyl group of which carbon number is
2 to 20, an aryl group of which carbon number is 6 to 14 or the like may
be used.

[0016]As the hydrocarbon group, specifically, a methyl group, an ethyl
group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl
group, a n-heptyl group, a n-octyl group, a n-nonyl group, a n-decyl
group, a n-dodecyl group, a tetradecyl group, a hexadecyl group, an
octadecyl group, an eicosyl group, a 2-propyl group, a 2-butyl group, a
2-methyl-2-propyl group, a 2-pentyl group, a 3-pentyl group, a 2-hexyl
group, a 3-hexyl group, a 2-octyl group, a 2-ethylhexyl group, a phenyl
group, a benzyl group or the like can be used. Also, as the hydrocarbon
group in which hydrogen atoms are replaced with fluorine atoms, for
example, there are a perfluoroalkyl group such as a nanofluorohexyl
group, a hexafluorohexyl group, a tridecafluorooctyl group, a
heptadecafluorooctyl group, a heptadecafluorodecyl group and the like,
obtained by replacing hydrogen atoms of the above-described hydrocarbon
groups with fluorine atoms in an arbitrary manner without particular
limits of the degree and location of replacement.

[0017]As specific examples of oxyalkylene group denoted by OA, of which
carbon number is 2 to 4 are alkylene oxide such as an oxyethylene group,
an oxytrimethylene group, an oxypropylene group, an oxybutylene group and
the like.

[0018]Note that the carbon number of the hydrocarbon group denoted as R is
preferably 1 to 12 in view of improving selectivity. Moreover, as for p,
a number of 0 to 6 is preferable and 0 is more preferable.

[0020]According to the present invention, types of water used for the
hydrolysis reaction of a raw material are not limited unless water
inhibits achievement of desired effects of the present invention. As such
water, for example, ion-exchange water, distilled water, reverse osmosis
filtered water and the like can be used. Within the range in which nature
of the present invention is not impaired, use of water containing salt
and the like such as tap water is no problem.

[0021]An amount of water with respect to an organic compound is not
particularly limited. However, in terms of molar conversion, it is
preferably 20 to 500 times as large as a stoichiometric amount of water
required for a reaction, more preferably 40 to 300 times as large as the
stoichiometric amount thereof, and furthermore preferable 70 to 200 times
as large as the stoichiometric amount thereof. In the above-described
range, a side reaction such as dimerization of an organic compound as a
raw material and a generated hydrolysate and the like can be suppressed
and thus the selectivity of the hydrolysate can be further increased.

[0022]In the production method according to the present invention, the
above-described organic compound as a raw material and water are mixed
and then a hydrolysis reaction is performed.

[0023]According to the present invention, mixing of an organic compound
and water and a hydrolysis reaction can be simultaneously performed in a
reactor (Aspect 1) or an organic compound and water may be mixed in a
mixer and then a hydrolysis reaction may be performed in a reactor
(Aspect 2). In Aspect 1, the reactor serves as a mixing section and a
reaction section, and in Aspect 2, the mixer corresponds to the mixing
section and the reactor corresponds to the reaction section.

[0024]Mixing of an organic compound and water is performed at a shear rate
(U/Dmin) of 5.5 (sec-1) or more, preferably at a shear rate (U/Dmin)
of 10 (sec-1) or more, more preferably at a shear rate (U/Dmin) of
20 (sec-1) or more, and further more preferably at a shear rate
(U/Dmin) of 100 (sec-1) or more. By performing shear flow of an
organic compound and water to mix the organic compound and water, the
organic compound and water can be reacted in a good mixed state through a
hydrolysis reaction. Accordingly, in Aspect 2, it is preferable that
after the mixture of the organic compound and water, the mixture is
quickly brought to a hydrolysis reaction while keeping the mixed state as
it is.

[0025]For shear rate U/Dmin, Dmin is a flow channel minimum inner diameter
(mm) and U is a flow rate (mm/sec) of the mixture of the organic compound
and water at Dmin. Assuming that the flow rate of the mixture is Q
(ml/sec), U (mm/sec) can be obtained based on the following formula (1)
where n is the number of the flow channel minimum inner diameter. For
example, when a porous contraction flow type mixer is used, n is the
number of pores in the mixer.

U (mm/sec)=Q×1000/(n×π×(Dmin)2/4) (1)

[0026]Moreover, a cross-sectional shape of the mixing portions does not
have to be a circular shape. When the cross-sectional shape is other than
a circular shape, U is a flow rate at a flow channel minimum
cross-sectional area. In that case, a diameter of a circle having the
same area as the flow channel minimum cross section is used as Dmin.

[0027]The flow channel minimum inner diameter of the mixing section is
preferably 1 mm or more in view of productivity and is preferable 15 mm
or less in view of achieving a good mixed state of an organic compound
and water. In consideration of these views, the flow channel minimum
inner diameter is preferably 1 to 15 mm and more preferably 1 to 10 mm.
The flow channel minimum inner diameter of the mixing section means the
flow channel minimum inner diameter of the mixer in Aspect 1 and also the
flow channel minimum inner diameter of the mixer in Aspect 2.

[0028]A mixing time is not particularly limited as long as the mixing time
is long enough to sufficiently mix an organic compound and water. In the
case of a continuous type mixer, in general, the mixing time is
preferably selected to be within the range from about 0.001 seconds to 10
hours. The range from about 0.001 seconds to 1 hour is more preferable
and the range from 0.001 seconds to 10 minutes is further more
preferable. The mixing time for a continuous type mixer means a time in
which a reaction liquid is retained in the mixer and is indicated by a
value obtained by dividing a volume of the mixer by a flow volume of
reaction materials supplied to the reactor per unit time.

[0029]In view of increasing reactivity of an organic compound and water
and in view of suppressing corrosion of a reactor, a reaction temperature
for a hydrolysis reaction is 150° C. to 350° C., preferably
200° C. to 300° C. and more preferably 250° C. to
290° C. As for a reaction pressure, a hydrolysis reaction is
performed under a condition where a pressure equal to or higher than a
saturation vapor pressure of water is applied and water can be kept to be
in a liquid state.

[0030]A reaction time varies depending on a reaction temperature, a type
of a raw material to be used and the like and therefore can not be
determined. However, in general, the reaction time is preferably selected
to be within the range from 0.1 minute to 10 hours. The range from 0.1
minute to 1 hour is more preferable and the range from 0.1 minute to 10
minutes is further more preferable. In the case of a batch type reactor,
the reaction time is counted from the completion of loading a raw
material and the like. In the case of a continuous type reactor, the
reaction time is counted from a timing at which a reaction has reached a
stationary state. The reaction time of the continuous type reactor means
a time in which a reaction liquid is retained in the reactor and is
indicated by a value obtained by dividing a volume of the reactor by a
flow volume of reaction materials supplied to the reactor per unit time.

[0031]According to the present invention, a hydrolysis reaction is
preformed at a high temperature. Thus, the reaction proceeds even without
a catalyst. However, an acid or alkali catalyst can be added. A catalyst
used in the present invention is not particularly limited but, for
example, an acid, a base or a combination of an acid and a base, which
are in general used in hydrolysis reaction, can be used.

[0032]When a catalyst is used, a usage amount of the catalyst is not
particularly limited as long as a desired reaction efficiency of a
hydrolysis reaction of a raw material is achieved. However, in general,
the usage amount is preferably 0.01 to 10 parts by weight and more
preferably 0.1 to 5 parts by weight with respect to 100 parts by weight
of an organic compound as a raw material.

[0033]As a mixer used for mixing an organic compound and water in advance,
in the case of a batch type mixer, for example, a propeller mixer, an
agihomo-mixer, a homo-mixer, a disk turbine paddle impeller having a high
shear property, a pitched blade paddle impeller, a paddle blade impeller
and the like can be preferably used. In the case of a continuous type
mixer, for example, a pipe line mixer, a line homo-mixer, an ultrasonic
mixer, a high pressure homogenizer, pumps such as a centrifugal pump
having a high shear property, a disper mixer, a static mixer and like can
be preferably used. Among the above-described examples, it is preferable
to use a static mixer because it has a simple configuration and its
maintenance can be done in a simple manner, compared to the other ones.
Specifically, an orifice contraction flow type mixer is more preferable
because a fluid shear rate at a mixing section thereof is high and high
mixing effect can be achieved.

[0034]A temperature when an organic compound and water are mixed in a
mixer is not particularly limited but is preferably about the same
temperature as a reaction temperature.

[0035]As a reactor for performing a hydrolysis reaction, in the case of a
continuous type reactor, a flow tube type reactor such as a tube type
reactor, a tower type reactor, a semi-batch reactor such as a continuous
stirred tank reactor and the like can be used.

[0036]In Aspect 1, the reactor serves as a mixing section and a reaction
section. In this case, mixing is performed by flow and diffusion of a
reaction liquid.

[0037]A material of the reactor used according to the present invention is
not particularly limited. In general, a material used for chemical
reaction can be arbitrarily used. Specific examples are metal materials
such as steel, stainless steel, Fe--Cr--Ni alloy such as carpenter 20 and
the like, copper alloy, aluminum alloy, Ni--Cr--Fe alloy, Ni--Cu alloy,
Ni--Mo--Fe--Cr alloy, cobalt alloy, titanium alloy, zirconium alloy,
molybdenum, chromium and the like, hard glass, silica glass, porcelain,
glass lining, synthetic resin, ceramic materials and the like. Among the
above-described materials, when a reaction takes place under a
temperature condition close to a supercritical water condition where
corrosion of materials is concerned, a metal material such as austenitic
stainless steel, Ni--Cr--Fe alloy, Ni--Mo--Fe--Cr alloy and the like is
preferable and Ni--Cr--Fe alloy and Ni--Mo--Fe--Cr alloy are more
preferable.

[0038]According to the method of the present invention, a hydrolysis
reaction can be performed by either one of a batch method in which a raw
material at a required amount for 1 batch is supplied and a hydrolysis
reaction for the amount is completed in a batch operation and a
continuous method in which a raw material is continuously supplied and a
hydrolysis reaction is performed. However, because a temperature can be
increased/reduced in a short time, reaction conditions can be controlled
in a simple manner and a reaction can be made to effectively proceed, it
is preferable to continuously perform a hydrolysis reaction.

[0039]When a hydrolysis reaction is continuously performed, a tube type
reactor is preferably used because it exhibits good operability and high
resistance to pressure in a high pressure reaction. Furthermore, when a
mixer is used, a static mixer is preferably used because it has a simple
configuration and its maintenance can be performed in a simple manner.
Specifically, an orifice contraction flow type mixer is more preferable
because a fluid shear rate at a mixing section thereof is high and high
mixing effect can be achieved.

[0040]After the completion of reaction, for example, a reacted mixture is
cooled down to a desired temperature, evaporation or distillation,
spontaneous sedimentation or centrifugal sedimentation or the like is
performed as desired according to a known method to refine the mixture
and separate the mixture from unreacted water, thus obtaining a
hydrolysate.

EXAMPLES

Example 1

[0041]A reaction apparatus shown in FIG. 1 was used. The reaction
apparatus of FIG. 1 includes a tube type reactor 1, a cooler 2, a raw
material supply section 3, a water supply section 4 and a separate
collection tank 5. Each of the raw material supply section 3 and the
water supply section 4 is connected to the tube type reactor 1.

[0042]After preheating to the same temperature as a reaction temperature,
2-ethyl-hexylglycidyl ether as a raw material and ion exchange water were
continuously supplied at 0.73 g/min and 7.03 g/min, respectively, from
the raw material supply section 3 and water supply section 4 to the tube
type reactor 1 (having a flow channel minimum inner diameter of 1.0 mm, a
tube length of 10 m and being formed of SUS316).

[0043]In the tube type reactor 1, an inner fluid was heated so that a
temperature (i.e., reaction temperature) of the inner fluid becomes
250° C., a pressure (i.e., reaction pressure) in the tube type
reactor 1 was controlled by a back pressure valve 6 so as to be 5 MPa.
Under the above-described temperature and pressure conditions, a
hydrolysis reaction of an organic compound as a raw material was
performed. The saturation vapor pressure of water at 250° C. was
4.0 MPa and the amount of water with respect to the organic compound as a
raw material in a stationary state of the reaction was, in terms of molar
conversion, 100 times as large as a stoichiometric amount of water
required for the reaction.

[0044]After the hydrolysis reaction, a resultant mixture was cooled down
to 40° C. to 50° C. in the cooler 2, and then the mixture
was collected in the separate collection tank 5 through the back pressure
valve 6. In the separate collection tank 5, the reacted mixture was split
into layers and a reactant as an upper layer was collected.

[0045]The reactant was sampled at one hour after glycidyl ether was
supplied and the hydrolysis reaction was started, and a reaction
conversion ratio and a dimer selective ratio for glyceryl ether were
obtained from a gas chromatogram (a gas chromatography apparatus: Agilent
6850 Series II manufactured by Agilent Technologies, a capillary column:
HP-ULTRA2 having dimensions of 12 m×0.2 mm×0.33 μm, an
internal standard substance: n-decan). Results are shown in Table 1. The
reaction conversion ratio was calculated based on: reacted glycidyl ether
(mol)/supplied glycidyl ether (mol)×100. The dimer production rate
indicating a side reaction was calculated based on: a dimer amount (mol
%) in the reactant/the reaction conversion ratio (mol %)×100.

Example 2

[0046]The tube type reactor 1 having a tube length of 3.1 m was used, the
reaction temperature was adjusted to be 270° C., the reaction
pressure was adjusted to be 7 MPa, 2-ethyl-hexylglycidyl ether as a raw
material was supplied at 0.23 g/min and ion exchange water was supplied
at 2.2 g/min. Other than that, in the same manner as in Example 1,
glyceryl ether was produced. Results are shown in Table 1. Note that a
saturation vapor pressure of water at 270° C. is 5.5 MPa.

Example 3

[0047]2-ethyl-hexylglycidyl ether as a raw material and ion exchange water
were continuously supplied at 1.64 g/min and 15.9 g/min, respectively, to
the tube type reactor 1 having a flow channel minimum inner diameter of
3.0 mm and a tube length of 2.0 m. Other than that, in the same manner as
in Example 2, glyceryl ether was produced. Results are shown in Table 1.

Example 4

[0048]The reaction temperature was adjusted to be 290° C. and the
reaction pressure was adjusted to be 9 MPa. Other than that, in the same
manner as in Example 3, glyceryl ether was produced. Results are shown in
Table 1. Note that a saturation vapor pressure of water at 290° C.
is 7.4 MPa.

Example 5

[0049]2-ethyl-hexylglycidyl ether as a raw material and ion exchange water
were continuously supplied at 18.17 g/min and 176 g/min, respectively, to
the tube type reactor 1 having a flow channel minimum inner diameter of
10 mm and a tube length of 2.0 m. Other than that, in the same manner as
in Example 4, glyceryl ether was produced. Results are shown in Table 1.

Example 6

[0050]A reaction apparatus shown in FIG. 2 was used. The apparatus of FIG.
2 includes a tube type reactor 1, a cooler 2, a raw material supply
section 3, a water supply section 4, a separate collection tank 5 and a
mixer 7. Each of the raw material supply section 3 and the water supply
section 4 is connected to the mixer 7.

[0051]After preheating to the same temperature as a reaction temperature,
2-ethyl-hexylglycidyl ether as a raw material and ion exchange water were
continuously supplied at 67.9 g/min and 657 g/min, respectively, from the
raw material supply section 3 and the water supply section 4 to the mixer
7. A contraction flow type mixer (in this case, Bunsan-kun manufactured
by Fujikin, including 5 pairs of 4-pore block and 5-pore block and having
a contraction section inner diameter of 1.0 mmφ and a pore length of
0.05 m) was provided in the mixer 7. Reaction materials mixed in the
mixer 7 were continuously supplied to the tube type reactor 1 (having a
flow channel inner diameter of 16 mm, a tube length of 5.4 m and being
formed of SUS316).

[0052]In the tube type reactor 1, an inner fluid was heated so that a
temperature (reaction temperature) of the inner fluid become 270°
C. and a pressure (i.e., reaction pressure) in the tube type reactor 1
was adjusted to be 7 MPa. Under the temperature and pressure conditions,
a hydrolysis reaction of an organic compound as a raw material was
performed. In a stationary state of a reaction, an amount of water with
respect to the organic compound as a raw material was, in terms of molar
conversion, 100 times as large as a stoichiometric amount of water
required for a reaction.

[0053]After the hydrolysis reaction, a mixture was cooled down to
40° C. to 50° C. in the cooler 2, and then the mixture was
collected in the separate collection tank 5 through the back pressure
valve 6. In the separate collection tank 5, the reacted mixture was split
into layers and a reactant as an upper layer was collected.

[0054]The reactant was sampled at one hour after glycidyl ether was
supplied and the hydrolysis reaction was started, and a reaction
conversion ratio and a dimer selective ratio for glyceryl ether were
obtained from the gas chromatogram. Results are shown in Table 1.

Example 7

[0055]The reaction temperature was adjusted to be 290° C., the
reaction pressure was adjusted to be 9 MPa and 2-ethyl-hexylglycidyl
ether as a raw material and ion exchange water were continuously supplied
at 102 g/min and 985 g/min, respectively, to the mixer 7. Other than
that, in the same manner as in Example 6, glyceryl ether was produced.
Results are shown in Table 1.

Example 8

[0056]2-ethyl-hexylglycidyl ether as a raw material and ion exchange water
were continuously supplied at 69.7 g/min and 472 g/min, respectively, to
the mixer 7. In a stationary state of a reaction, an amount of water with
respect to the organic compound as a raw material was, in terms of molar
conversion, 70 times as large as a stoichiometric amount of water
required for a reaction. Other than that, as in the same manner as in
Example 6, glyceryl ether was produced. Results are shown in Table 1.

Example 9

[0057]2-ethyl-hexylglycidyl ether as a raw material and ion exchange water
were continuously supplied at 26.9 g/min and 520 g/min, respectively, to
the mixer 7. In a stationary state of a reaction, an amount of water with
respect to the organic compound as a raw material was, in terms of molar
conversion, 200 times as large as a stoichiometric amount of water
required for a reaction. Other than that, as in the same manner as in
Example 8, glyceryl ether was produced. Results are shown in Table 1.

Example 10

[0058]The tube type reactor 1 having a tube length of 10.8 m was used,
isodecylglycidyl ether as a raw material and ion exchange water were
supplied at 77.0 g/min and 647 g/min, respectively, to the mixer 7, the
reaction temperature was adjusted to be 280° C. and the reaction
pressure was adjusted to be 8 MPa. Other than that, in the same manner as
in Example 6, glyceryl ether was produced. Results are shown in Table 1.
Note that a saturation vapor pressure of water at 280° C. is 6.4
MPa.

Example 11

[0059]The reaction apparatus of FIG. 2 was used. After preheating to the
same temperature as a reaction temperature, 2-ethyl-hexylglycidyl ether
as a raw material and ion exchange water were continuously supplied at
4650 g/min and 45000 g/min, respectively, to the mixer 7. A contraction
flow type mixer (in this case, Bunsan-kun manufactured by Fujikin,
including 5 pairs of 20-pore block and 25-pore block and having a
contraction section inner diameter of 3.0 mmφ and a pore length of
0.05 m) was provided in the mixer 7. Reaction materials mixed in the
mixer 7 were continuously supplied to the tube type reactor 1 (having a
flow channel inner diameter of 50 mm and a tube length of 74 m).

[0060]In the tube type reactor 1, an inner fluid was heated so that the
reaction temperature become 250° C. and the reaction pressure was
adjusted to be 8 MPa. Under the temperature and pressure conditions, a
hydrolysis reaction of an organic compound as a raw material was
performed. Results are shown in Table 1.

Comparative Example 1

[0061]Instead of the reaction apparatus of FIG. 2, the reaction apparatus
of FIG. 1 was used. That is, the mixer 7 was not used. Other than that,
in the same manner as in Example 6, glyceryl ether was produced. Results
are shown in Table 1.

Comparative Example 2

[0062]Instead of the reaction apparatus of FIG. 2, the reaction apparatus
of FIG. 1 was used. That is, the mixer 7 was not used. Other than that,
in the same manner as in Example 8, glyceryl ether was produced. Results
are shown in Table 1.

Comparative Example 3

[0063]Instead of the reaction apparatus of FIG. 2, the reaction apparatus
of FIG. 1 was used. That is, the mixer 7 was not used. Other than that,
in the same manner as in Example 9, glyceryl ether was produced. Results
are shown in Table 1.

Comparative Example 4

[0064]Instead of the reaction apparatus of FIG. 2, the reaction apparatus
of FIG. 1 was used. That is, the mixer 7 was not used. Other than that,
in the same manner as in Example 10, glyceryl ether was produced. Results
are shown in Table 1.

[0065]In each of Examples 1 through 5 and Comparative Examples 1 through
4, a reactive apparatus which does not include the mixer 7 was used.
However, the reactor 1 serves as a mixing section and a reaction section.

[0066]According to the results described above, compared to the
comparative examples, in each of the Examples, the conversion ratio is
high and the dimer selective ratio is low. This shows that a hydrolysis
reaction was efficiently performed.

INDUSTRIAL APPLICABILITY

[0067]As has been described, the present invention is useful as a method
for producing a hydrolysate, in which an organic compound and water are
mixed and a hydrolysis reaction of the organic compound is performed. A
hydrolysate obtained according to the present invention, e.g., glyceryl
ether obtained by hydrolysis of glycidyl ether can be used as a solvent,
an emulsifier, a dispersant, a detergent, a foam booster and the like.